Cilomilast

Names

[ Name ]:
Cilomilast

[Synonym ]:
cis-4-(3-(Cyclopentyloxy)-4-methoxyphenyl)-4-cyanocyclohexane-1-carboxylic acid
Cyclohexanecarboxylic acid, 4-cyano-4-(3-(cyclopentyloxy)-4-methoxyphenyl)-, cis-
1xlx
Cyclohexanecarboxylic acid, 4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-, cis-
cis-4-Cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexanecarboxylic acid
cis-4-Cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexanecarboxylic acid
S1455_Selleck
Ariflo
Cyclohexanecarboxylic acid, 4-cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-
c-4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-r-1-cyclohexane carboxylic acid
1xom
cilomilast
4-Cyano-4-[3-(cyclopentyloxy)-4-methoxyphenyl]cyclohexanecarboxylic acid
SB-207499

Biological Activity

[Description]:

Cilomilast(SB 207499; Ariflo) is a potent PDE4 inhibitor with IC50 of about 110 nM, has anti-inflammatory activity and low central nervous system activity.IC50 value: 110 nMTarget: PDE 4Cilomilast (SB-207499) inhibits HPDE4 and LPDE4 catalytic activity with equal potency (Ki ≈100 nM). SB-207499 and rolipram are equipotent against LPDE4, but Cilomilast (Ariflo, SB-207499) is 100-fold less potent against HPDE4. This profile suggests that Cilomilast (Ariflo, SB-207499) retain the anti-inflammatory activity of rolipram yet have a decreased tendency to produce side effects.

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphodiesterase (PDE)

Research Areas >> Inflammation/Immunology

[References]

[1]. MARY S. BARNETTE et al. SB 207499 (Ariflo), a Potent and Selective Second-Generation Phosphodiesterase 4 Inhibitor: In Vitro Anti-inflammatory Actions JPET 284:420 -426, 1998

[2]. Munisso MC, Kang JH, Tsurufuji M, Yamaoka T.Cilomilast enhances osteoblast differentiation of mesenchymal stem cells and bone formation induced by bone morphogenetic protein 2.Biochimie. 2012 Jun 15.

[3]. Sadrai Z, Stevenson W, Okanobo A, Chen Y, Dohlman TH, Hua J, Amparo F, Chauhan SK, Dana R.PDE4 inhibition suppresses IL-17-associated immunity in dry eye disease.Invest Ophthalmol Vis Sci. 2012 Jun 14;53(7):3584-91. Print 2012 Jun.

[4]. Pace E, Ferraro M, Uasuf CG, Giarratano A, La Grutta S, Liotta G, Johnson M, Gjomarkaj M.Cilomilast counteracts the effects of cigarette smoke in airway epithelial cells.Cell Immunol. 2011;268(1):47-53. Epub 2011 Feb 20.

[5]. Barton AK, Niedorf F, Gruber AD, Kietzmann M, Ohnesorge B.Pharmacological studies of bronchial constriction inhibited by parasympatholytics and cilomilast using equine precision-cut lung slices.Berl Munch Tierarztl Wochenschr. 2010 May-Jun;123(5-6):229-35

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
549.1±50.0 °C at 760 mmHg

[ Melting Point ]:
157ºC

[ Molecular Formula ]:
C₂₀H₂₅NO₄

[ Molecular Weight ]:
343.417

[ Flash Point ]:
285.9±30.1 °C

[ Exact Mass ]:
343.178345

[ PSA ]:
79.55000

[ LogP ]:
3.30

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.568

[ Storage condition ]:
?20°C

[ Water Solubility ]:
DMSO: soluble15mg/mL, clear

MSDS

Click to get detail MSDS

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Blockade of PDE4B limits lung vascular permeability and lung inflammation in LPS-induced acute lung injury.

Biochem. Biophys. Res. Commun. 450(4) , 1560-7, (2014)

Acute lung injury (ALI), acute respiratory distress syndrome (ARDS), is actually involved in an ongoing and uncontrolled inflammatory response in lung tissues. Although extensive studies suggested tha...